Triethylamine → 4-Amino-3-chloro-N,N-dimethylbenzamide

HRID 529648

反応式

HRID 529648 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].Cl.[CH3:13][N:14](C)[CH2:15]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNC>C(Cl)Cl.C(O)(C)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([CH3:15])[CH3:13])=[O:7])=[CH:4][C:3]=1[Cl:11]

参加物

9

反応物 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 202874814-Amino-3-chloro-N,N-dimethylbenzamide収率 59.6%

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-amino-3-chloro-benzoic acid (1 equiv) in DCM (0.12 M) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 equiv), 1-hydroxybenzotriazole (1.2 equiv), triethylamine (4 equiv) and dimethylamine hydrochloride (2 equiv) sequentially. The mixture was stirred at room temperature overnight. After the reaction was complete, as monitored by LCMS, the mixture was diluted with a mixture of isopropanol in chloroform (30%,), washed with water and dried over anhydrous sodium sulfate. The organic phase was concentrated and the residue obtained was recrystallized in the mixture of hexane and ethyl acetate (10%,) to afford the desired product (Yield: 59.6%) as a light brown solid. MS (ESI) m/z 199.1 [M+1]+.

後処理

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic phase was concentrated
  4. customthe residue obtained
  5. customwas recrystallized in the mixture of hexane and ethyl acetate (10%,)

出典と根拠

ORDレコード
ord-0187656467444a3f8b52cea66baa6d74
出典データセット
uspto-grants-2016_05
特許番号
US09346812B2

関連ノート

読み込み中…